Sulfuric Acid → 2-(4-Chloro-3-difluoromethoxy-2-pyridyl)-2-cyclopropylethanal

HRID 1061468Notes

Reaction equation

HRID 1061468 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([CH:12]2[CH2:14][CH2:13]2)=[CH:9][O:10]C)[C:3]=1[O:15][CH:16]([F:18])[F:17].S(=O)(=O)(O)O>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]([CH:12]2[CH2:13][CH2:14]2)[CH:9]=[O:10])[C:3]=1[O:15][CH:16]([F:18])[F:17]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 865864702-(4-Chloro-3-difluoromethoxy-2-pyridyl)-2-cyclopropyl-1-methoxyethene

Product 1

HCID 186293232-(4-Chloro-3-difluoromethoxy-2-pyridyl)-2-cyclopropylethanalYield 56.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

130 mg of 2-(4-chloro-3-difluoromethyl-2-pyridyl)-2-cyclopropyl-1-methoxyethene (XI) was dissolved in 10 ml of THF, which was added 3 ml of dilute sulfuric acid and concentrated at 50° C. under reduced pressure. The resulting mixture was poured into water and neutralized with saturated sodium bicarbonate solution, and thereafter, extracted with chloroform. The resulting organic layer was washed with saturated salt water, and thereafter, dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 70 mg of 2-(4-chloro-3-difluoromethyl-2-pyridyl)-2-cyclopropylethanal (XII).

Workup

  1. concentrationconcentrated at 50° C. under reduced pressure
  2. additionThe resulting mixture was poured into water and neutralized with saturated sodium bicarbonate solution
  3. extractionextracted with chloroform
  4. washThe resulting organic layer was washed with saturated salt water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-6b18edbb1dd74d8ab28c971c0da11d64
Source dataset
uspto-grants-2003_02
Patent number
US06525066B2

Reaction notes

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